Winter Garden › Oakland Area
The Oakland Area of Winter Garden
Known as one of the hidden gems of Florida, Oakland is surrounded by moss-draped oak trees and found on the shores of Lake Apopka. It's a naturally beautiful area of Winter Garden boasting waterfront properties within a serene setting nestled in the Northwestern area of Winter Garden just before Clermont off Hwy 50 in West Orange County.
The Oakland Nature Preserve
One of the best attractions found in Oakland is the Oakland Nature Preserve. Since 1999, this preserve has been providing education to visitors about the native flora and fauna, while providing conservation efforts for the area land. Its open year-round and there's no charge to enjoy the preserve. 
The Nature Preserve provides plenty of fun with 128 acres of space for environmental education and recreation. It's a popular spot for field trips and summer camps. Many visitors come for the guided tours, hiking trails and special events.
The Boardwalk also attracts many visitors. It's the most popular trail on the preserve and takes you through shaded wetlands to a covered pavilion with views of Lake Apopka. Interpretive signage is found throughout to identify trees and plants. Often, you will spot turtles, alligators and wading birds from the Boardwalk.
Lake Apopka
Another huge part of the culture and recreation of Oakland, Florida is Lake Apopka. It's the second largest lake in the entire state and used to be known as the bass fishing capital of the entire southern United States. The lake is fed by a natural spring and covers about 30,800 acres of surface area.
The Oakland Heritage Festival
One of the largest and most popular events held annually in Oakland is the Heritage Festival. This festival provides plenty of fun with more than 2,000 attendees and over 50 vendors every year. It's held at Speer Park in Oakland and helps to support the Oakland Nature Preserve.
Those attending the event get to enjoy hayride tours, a silent auction, boat tours, live music, a number of great speakers, a petting zoo and so much more. There are crafts and activities specifically for children and even some of the more exotic animals on hand. The festival is held in October every year.
Oakland Avenue Charter School
Along with the beautiful nature of the area, Oakland, Florida is home to a 700-student charter elementary school. This school provides a choice for residents with school-aged children outside of the public schools serving the community.
Real Estate in Oakland
A variety of housing options are found in Oakland with homes ranging from about $200K up to more than $1 million. The area does have some undeveloped land for those looking to create a new construction home and there are plenty of waterfront homes and lots available, as well.
Some of the finer waterfront estates provide incredible views of Lake Apopka and may even provide private docks. Oakland attracts a variety of home buyers due to the range of options and prices.
Neighborhoods in the Oakland Area include:
Oakland Florida Homes for Sale
Pre-Construction. To be built. Future Medical, Profesional Office and Retail Plaza to feature a mixture of office and retail spaces. A project of over48,000 sqf. of buil...
- Tucker Oaks SubDv.
- 34787 Zip Code
COMMERCIAL 5 (+-) ACRES DIRECT HWY 50 FRONTAGE. SEE SURVEY IN PHOTOS, HIGH TRAFFIC AREA WITH RED LIGHT AND ROAD ON EACH SIDE. GROWTH AREA WITH MANY OPPORTUNITIES, FUTUR...
- 34787 Zip Code
Pre-Construction. To be built. Pre-Construction. To be Built. Here is your chance to design and build your dream CUSTOM MODERN FARMHOUSE in one Winter Gardens Premier co...
- 4 Beds
- 5 Baths
- Oakland Hills SubDv.
- 34787 Zip Code
Pre-Construction. To be built. Fall in love with this modern farmhouse masterpiece within Winter Garden’s premier luxury new home community, Oakland Hills! Unlike anythin...
- 4 Beds
- 4 Baths
- Oakland Hills SubDv.
- 34787 Zip Code
These five plus acre are adjacent to a newly developed area of homes ranging in the 400,000 value. The property sits at the end of a cul-de-sac within this development. T...
- 34787 Zip Code
These six plus acre are adjacent to a newly developed area of homes ranging in the 400,000 value. The property sits at the end of a cul-de-sac within this development. Th...
- 34787 Zip Code
Welcome to Lake Living! This custom home located in gated Deer Island has so much to offer in Outdoor living and entertainment space with room to grow. Open floor plan,...
- 3 Beds
- 2.5 Baths
- Deer Island SubDv.
- 34787 Zip Code
STUNNING TRANSITIONAL MASTERPIECE IN DESIRABLE OAKLAND PARK. Located just down from the quaint streets of Winter Garden’s historic district with boutique shoppes, restaur...
- 5 Beds
- 4.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Location, Location, Location. This magnificent home in Winter Garden is located in the private gated sought-after community of Deer Island, which is surrounded by John’s ...
- 4 Beds
- 4 Baths
- Deer Island Ph 02 SubDv.
- 34787 Zip Code
Under Construction. Contemporary design and classic appeal blend to create the brilliant Seaside dream home plan. Your open floor plan provides a sensational expanse of e...
- 4 Beds
- 3.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Beautiful custom built 3/2.5 home by award winning J&J Building. This POOL home is located in the highly sought after Oakland Park community! The Craftsman style home is ...
- 3 Beds
- 2.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Picture-perfect farmhouse in the PARADE of HOMES winning community, Oakland Park! Located just footsteps to PARKS, trails, water views, the resort style POOL and clubhou...
- 4 Beds
- 3 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Pre-Construction. To be built. Pre-Construction. This Florida Vernacular style Design-Ready home, The Jackson, includes a trendy metal roof over the front porch, 8' inter...
- 4 Beds
- 3 Baths
- Oakland Park SubDv.
- 34787 Zip Code
This PARK front home in OAKLAND PARK is just footsteps away from the LAKEFRONT walking trail, Community Clubhouse, and RESORT style POOL! The model features 4 bedrooms (m...
- 4 Beds
- 2.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Under Construction. This Florida Vernacular style Quick Move-In home, The Jackson, includes a trendy metal roof over the front porch, 8' interior doors and 10' ceilings o...
- 3 Beds
- 2.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Under Construction. Exquisite refinements and innovative comforts combine in The Stoneycreek family home plan. Vibrant space , an abundance of natural light, and limitles...
- 4 Beds
- 4 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Under Construction. Welcome exceptional elegance and innovative comforts to your life in the beautiful Stoneycreek home plan. Conversations with loved ones and quiet even...
- 4 Beds
- 3.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Under Construction. This new home in Oakland is a single-story, 3-way-split plan with 4 bedrooms and 3 baths. Find a bedroom with its own full bath right off the foyer at...
- 4 Beds
- 3 Baths
- Hull Island SubDv.
- 34787 Zip Code
Under Construction. Experience the lifestyle benefits of brilliant craftsmanship and timeless beauty in The Pascal new home plan. The spacious study presents a versatile ...
- 3 Beds
- 2.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
One or more photo(s) has been virtually staged. Come see this one-of-a-kind, beautiful 5-bedroom, 3-bathroom custom built home on a 0.3-acre corner lot in the heart of qu...
- 5 Beds
- 3 Baths
- Oakland Pointe SubDv.
- 34760 Zip Code
Welcome to this charming historical 3 bed, 3 bath home located a heartbeat from Downtown Winter Garden. Surrounded by hundred-year-old oak trees, you have a unique opport...
- 3 Beds
- 3 Baths
- N/A SubDv.
- 34787 Zip Code
Under Construction. Experience the brilliant craftsmanship and timeless style in The Barksdale dream home plan. Create a welcoming lounge or a quiet home office in the ve...
- 3 Beds
- 2.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Under Construction. Under Construction! Stunning Summerlin floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85...
- 5 Beds
- 4.5 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Large 4 Bedroom 2 Bathroom 3-way split floor plan with an Office and a 2 car Garage. Exclusively located in a gated community with easy access to Florida's Turnpike, 408,...
- 4 Beds
- 2 Baths
- Johns Cove 43/104 SubDv.
- 34787 Zip Code
Under Construction. Under Construction! Stunning Portland floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...
- 4 Beds
- 3.5 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Under Construction! Stunning Portland floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...
- 4 Beds
- 3.5 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Stylish Courtyard home was recently completed, and it's a perfect SINGLE FAMILY HOME, OR SECOND RESIDENCE, OR INVESTMENT! Located in the much desired MCKINNON SQUARE at O...
- 3 Beds
- 2.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Under Construction. Stunning Camden floor plan located in the highly sought after community of Lake Apopka Sound. Featuring a rare Multi-Generational site with a private ...
- 4 Beds
- 3.5 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Stunning Camden floor plan located in the highly sought after community of Lake Apopka Sound. Featuring a rare Multi-Generational site with a private ...
- 4 Beds
- 3.5 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
RARE CONSERVATION VIEWS in Lake front Hull Island community just minutes from picturesque downtown Winter Garden. This 4 bed, 3 bath home is a rare find with incredible...
- 4 Beds
- 3 Baths
- Hull Island At Oakland SubDv.
- 34787 Zip Code
Under Construction. Under Construction! Stunning Robinson floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...
- 4 Beds
- 3 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Charming Destin floor plan located in the highly sought after community of Lake Apopka Sound. This open design concept offers ample entertaining and l...
- 4 Beds
- 3.5 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Under Construction! Stunning Robinson floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...
- 4 Beds
- 3 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Charming Destin floor plan located in the highly sought after community of Lake Apopka Sound. This open design concept offers ample entertaining and l...
- 4 Beds
- 3.5 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Charming Destin floor plan located in the highly sought after community of Lake Apopka Sound. This open design concept offers ample entertaining and l...
- 4 Beds
- 3.5 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Charming Destin floor plan located in the highly sought after community of Lake Apopka Sound. This open design concept offers ample entertaining and l...
- 4 Beds
- 3 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Under Construction: This Charming Destin floor plan located in the highly sought after community of Lake Apopka Sound. This open design concept offers...
- 4 Beds
- 3.5 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. **Under Construction **Charming Destin floor plan located in the highly sought after community of Lake Apopka Sound. This open design concept offers a...
- 4 Beds
- 3 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Charming Robinson floor plan located in the highly sought after community of Lake Apopka Sound. This open design concept offers ample entertaining and...
- 4 Beds
- 3 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Under Construction! Stunning Robinson floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...
- 4 Beds
- 3 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Under Construction! Stunning Robinson floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...
- 4 Beds
- 3 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Under Construction! Stunning Robinson floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...
- 4 Beds
- 3 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Under Construction. Charming Robinson floor plan located in the highly sought after community of Lake Apopka Sound. This open design concept offers ample entertaining and...
- 4 Beds
- 3 Baths
- Lake Apopka Sound SubDv.
- 34787 Zip Code
Beautiful 3 bed 2 bath home set on end lot in a cul de sac located in the town of Oakland. This is Pulte Arbordale Floor plan with so many upgrades. This home offers sola...
- 3 Beds
- 2 Baths
- Longleaf/Oakland Rep SubDv.
- 34787 Zip Code
Under Construction. The Kelsey new home plan combines elegance, comfort, and top-quality craftsmanship. Escape to the serenity of your Owner’s Retreat, which includes a c...
- 3 Beds
- 2.5 Baths
- Oakland Park SubDv.
- 34787 Zip Code
Totally renovated 3 bedroom, 2 bathroom home located in the heart of Oakland with private sweeping views of the nature preserve! This home has brand new flooring througho...
- 3 Beds
- 2 Baths
- Trailside Station Rep 44/23 SubDv.
- 34787 Zip Code
Welcome to OAKLAND. NO HOA!!!! This spacious home with an additional detached two car garage is steps away from the West Orange Trail, 2 minutes from the much desired DOW...
- 3 Beds
- 2 Baths
- Hull Island Reserve 50 48 SubDv.
- 34787 Zip Code
One or more photo(s) has been virtually staged. Fantastic 3 bedroom home in sought after Oakland location. The impeccable kitchen has beautiful quartz counters, stylish t...
- 3 Beds
- 2 Baths
- Oakland Trls Ph 2 SubDv.
- 34787 Zip Code
Gorgeous Oakland Trails home with ALL of the bells and whistles! Situated on a premium, large lot on the highly-coveted "inner loop," this home boasts head-to-toe stone f...
- 3 Beds
- 2.5 Baths
- Oakland Trails Ph 1 SubDv.
- 34787 Zip Code
Exclusive Deer Island Gated Community - Waterfront Homesite - with incredible views and private boat dock capability on John’s Lake. Why settle for as-built when you can...
- Deer Island SubDv.
- 34787 Zip Code
Immaculately maintained 2 year old townhome located in the quaint town of Oakland. This 2 bed 2 ½ bath Townhome with covered front porch home shows like a Model Home and...
- 2 Beds
- 2.5 Baths
- Longleaf/Oakland Rep SubDv.
- 34787 Zip Code
LOCATED NEAR DOWNTOWN WINTER GARDEN, CLOSE TO THE WINTER GARDEN TRAIL, PLANT STREET, TURNIPIKE AND MUCH MORE. HOUSE OFFERS A 3 BEDROOMS AND 2 AND 1/2 BATH WITH LOTS OF UP...
- 3 Beds
- 2.5 Baths
- Longleaf/Oakland Rep SubDv.
- 34787 Zip Code
One or more photo(s) has been virtually staged. Your dream home is waiting just for you in Winter Garden! Enjoy preparing meals in this impressive kitchen equipped with a...
- 3 Beds
- 2.5 Baths
- Villas/Tucker Oaks SubDv.
- 34787 Zip Code
WOW! An unbelievable renovation with 2022 designer finishes throughout! Three bed/two and a half bath/two car garage. Turn-key, move-in ready in a gated community. Beauti...
- 3 Beds
- 2.5 Baths
- Tucker Oaks SubDv.
- 34787 Zip Code
Welcome to Tucker Oaks and this move in ready 3 bedroom 2 1/2 bath condo waiting for it’s next family. Recently painted and has brand new carpet upstairs. Open concept wi...
- 3 Beds
- 2.5 Baths
- Tucker Okas SubDv.
- 34787 Zip Code
Location and Amenities! Welcome to Tucker Oaks in Winter Garden, a gated community. This Unit is well-maintained and move-in ready. juts add your special touch. You will ...
- 3 Beds
- 2.5 Baths
- Tucker Oaks SubDv.
- 34787 Zip Code
Huge residential lot in desirable Winter Garden. Lot is located in a quiet unpaved road with a ranch type home as your only neighbor. Back part of lot overlooks virgin wo...
- Acreage SubDv.
- 34787 Zip Code
Welcome to the best kept secret in all of Winter Garden! Johns Lake Homesites subdivision offers tree-lined streets with mature LIVE OAK trees, breathtaking SUNSET views...
- Johns Lake Homesites Add 01 SubDv.
- 34787 Zip Code
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Downtown Winter Garden Area Neighborhoods
- Downtown Winter Garden
- Brandy Creek
- Chapin Station
- Courtlea Oaks
- Courtlea Park
- Covington Chase
- Crown Point Springs
- Daniels Crossing
- Fullers Crossing
- Fullers Landing
- Heritage at Plant Street
- Island Pointe
- Kings Bay
- Lake Cove Pointe
- Lakeview Reserve
- Magnolia Wood
- McAllister Landing
- Oakglen Estates
- Oaks at Brandy Lake
- Park Place
- Regal Pointe
- Stanton Estates
- Sterling Pointe
- Timbercreek Pines
- Traditions
- Trails of Winter Garden
- Tuscany
- Walkers Grove
- Winter Oaks
Winter Garden Village Area Neighborhoods
- Alexander Ridge
- Amberleigh
- Avalon Reserve
- Avalon Ridge (NEW)
- Banana Bay Estates
- Bay Isle
- Belle Meade
- Black Lake Park
- Black Lake Preserve
- Bradford Creek
- Bronsons Landing
- Canopy Oaks
- Carriage Pointe
- Cobblestone
- Country Lakes
- Cypress Reserve
- Daniels Landing
- Deerfield Place
- Emerald Ridge
- Foxcrest
- Glynwood
- Grove Park
- Grovehurst
- Hickory Hammock
- Johns Lake Pointe
- Lake Roberts Landing
- Orange Cove
- The Orchard
- Oxford Chase
- Regency Oaks
- Reserve at Carriage Pointe
- Roper Reserve
- Sanctuary at Twin Waters
- Southern Pines
- Stone Creek
- Stoneybrook West
- Sunset Lakes
- Tilden Place
- Twinwaters
- Waterside
- Westfield Lakes
- Windermere Crossing
- Windward Cay
- Wintermere Harbor
- Wintermere Pointe
- Woodbridge on the Green
Horizon West Area Neighborhoods
- Avalon Cove
- Cove At Hamlin
- Enclave at Hamlin
- Encore at Ovation
- Hamilton Gardens
- Hamlin Reserve
- Hawksmoor
- Highland Ridge (NEW)
- Highlands Summerlake
- Independence
- Isles Of Lake Hancock
- Lake Hancock Preserve
- Lakeshore
- Lakeside at Hamlin
- Lakeview Pointe
- Lakeview Preserve
- Latham Park
- Mezzano (NEW)
- Orchard Hills
- Orchard Park
- Osprey Ranch (NEW)
- Overlook At Hamlin
- Panther View
- Ravenna
- Sanctuary at Hamlin
- Storey Grove
- Summerlake
- Summerlake Groves
- Waterleigh
- Watermark
- Westhaven Ovation (NEW)
- Wincey Groves
- Winding Bay
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